Bicyclic indazole amides of Formula (1) are described in WO 2005/063767, WO 2005/092890, WO 2005/111038, WO 2006/001894 and WO 2006/069097
wherein    R1 is
                wherein        R2 is H, or C1-4-alkyl (e.g., CH3) which is unsubstituted or substituted one or more by F, Cl, Br, I, CN, OH, alkoxy having 1 to 4 carbon atoms (e.g., OCH3), NR4R5, or combinations thereof;        R4 and R5 are each independently H or Ar, Ar—C1-4-alkyl, Het, C1-4-alkyl (e.g., CH3), C3-8-cycloalkyl (e.g., cyclopropyl), or C4-8-cycloalkylalkyl (e.g., cyclopropylmethyl), each of which is unsubstituted or substituted one or more times by F, Cl, Br, I, CN, OH, alkoxy having 1 to 4 carbon atoms (e.g., OCH3), monoalkylamino, dialkylamino (e.g., diethylamino), C3-8-cycloalkyl, or combinations thereof,        and        m is 1, 2 or 3;or            R1 is A1, wherein A1 is
                wherein R6 to R14 are each, independently,        H,        C1-4-alkyl (e.g., CH3) which is unsubstituted or substituted one or more times by F, Cl, Br, I, CN, alkoxy having 1 to 4 carbon atoms (e.g., OCH3), Ar (e.g., phenyl) or combinations thereof,        C3-6-alkenyl which is unsubstituted or substituted one or more times by F, Cl, Br, I, CN, alkoxy having 1 to 4 carbon atoms (e.g., OCH3), Ar (e.g., phenyl) or combinations thereof,        C3-6-alkynyl which is unsubstituted or substituted one or more times by F, Cl, Br, I, CN, alkoxy having 1 to 4 carbon atoms (e.g., OCH3), or Ar (e.g., phenyl) or combinations thereof,        cycloalkyl having 3 to 10, preferably 3 to 8 carbon atoms, which is unsubstituted or substituted one or more times by halogen, hydroxy, oxo, cyano, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, or combinations thereof (e.g., cyclopentyl),        cycloalkylalkyl having 4 to 16, preferably 4 to 12 carbon atoms, which is unsubstituted or substituted in the cycloalkyl portion and/or the alkyl portion one or more times by halogen, oxo, cyano, hydroxy, C1-4-alkyl, C1-4-alkoxy or combinations thereof (e.g., cyclopentylmethyl, cyclopropylmethyl, etc.),        Ar-alkyl (e.g., benzyl), or        Het-alkyl (e.g., thienylmethyl);        wherein        Ar                    is an aryl group containing 6 to 10 carbon atoms which is unsubstituted or substituted one or more times by                            alkyl having 1 to 8 carbon atoms,                alkoxy having 1 to 8 carbon atoms,                halogen (F, Cl, Br, or I, preferably F or Cl),                amino,                cyano,                hydroxyl,                nitro,                halogenated alkyl having 1 to 8 carbon atoms,                halogenated alkoxy having 1 to 8 carbon atoms,                hydroxyalkyl having 1 to 8 carbon atoms,                hydroxyalkoxy having 2 to 8 carbon atoms,                alkenyloxy having 3 to 8 carbon atoms,                monoalkylamino having 1 to 8 carbon atoms,                dialkylamino wherein the alkyl portions each have 1 to 8 carbon atoms,                carboxy,                alkoxycarbonyl,                alkylaminocarbonyl,                acylamido (e.g., acetamido),                acyloxy (e.g., acetoxy),                alkylthio having 1 to 8 carbon atoms,                alkylsulphinyl having 1 to 8 carbon atoms,                alkylsulphonyl having 1 to 8 carbon atoms,                sulfo,                sulfonylamino,                Het,                cycloalkylamino wherein the cycloalkyl group has 3 to 7 carbon atoms and is optionally substituted by halogen (F, Cl, Br, or I, preferably F or Cl), alkyl having 1 to 8 carbon atoms, halogenated alkyl having 1 to 8 carbon atoms, alkoxy having 1 to 4 carbon atoms, amino, monoalkylamino wherein the alkyl portion has 1 to 8 carbon atoms, dialkylamino wherein the alkyl portions each have 1 to 8 carbon atoms, COR17, CSR17, cyano, hydroxyl, nitro, oxo, or thio,                aryloxy wherein the aryl portion contains 6 to 10 carbon atoms (e.g., phenyl, naphthyl, biphenyl) and is optionally substituted by halogen (F, Cl, Br, or I, preferably F or Cl), alkyl having 1 to 8 carbon atoms, halogenated alkyl having 1 to 8 carbon atoms, alkoxy having 1 to 4 carbon atoms, amino, monoalkylamino wherein the alkyl portion has 1 to 8 carbon atoms, dialkylamino wherein the alkyl portions each have 1 to 8 carbon atoms, COR17, CSR17, cyano, hydroxyl, nitro, oxo, or thio,                arylthio wherein the aryl portion contains 6 to 10 carbon atoms (e.g., phenyl, naphthyl, biphenyl) and is optionally substituted by halogen (F, Cl, Br, or I, preferably F or Cl), alkyl having 1 to 8 carbon atoms, halogenated alkyl having 1 to 8 carbon atoms, alkoxy having 1 to 4 carbon atoms, amino, monoalkylamino wherein the alkyl portion has 1 to 8 carbon atoms, dialkylamino wherein the alkyl portions each have 1 to 8 carbon atoms, COR17, CSR17, cyano, hydroxyl, nitro, oxo, or thio,                cycloalkyloxy wherein the cycloalkyl group has 3 to 7 carbon atoms and is optionally substituted by halogen (F, Cl, Br, or I, preferably F or Cl), alkyl having 1 to 8 carbon atoms, halogenated alkyl having 1 to 8 carbon atoms, alkoxy having 1 to 4 carbon atoms, amino, monoalkylamino wherein the alkyl portion has 1 to 8 carbon atoms, dialkylamino wherein the alkyl portions each have 1 to 8 carbon atoms, COR17, CSR17, cyano, hydroxyl, nitro, oxo, or thio, or                                    combinations thereof;                        Ar-alkyl                    is an aryl-alkylene group (e.g., benzyl, phenethyl, phenpropyl) wherein the alkylene portion contains 1 to 4 carbon atoms and is unsubstituted or substituted one or more times by halogen (F, Cl, Br, or I, preferably F or Cl), alkyl having 1 to 8 carbon atoms, halogenated alkyl having 1 to 8 carbon atoms, alkoxy having 1 to 4 carbon atoms, amino, monoalkylamino wherein the alkyl portion has 1 to 8 carbon atoms, dialkylamino wherein the alkyl portions each have 1 to 8 carbon atoms, COR17, CSR17, cyano, hydroxyl, nitro, oxo, or thio, and the aryl portion is Ar as defined above; and                        Het                    is a heterocyclic group, which is fully saturated, partially saturated or fully unsaturated, having 5 to 10 ring atoms in which at least 1 ring atom is a N, O or S atom, which is unsubstituted or substituted one or more times by                            alkyl having 1 to 8 carbon atoms,                alkoxy having 1 to 8 carbon atoms,                halogen (F, Cl, Br, or I, preferably F or Cl),                amino,                cyano,                hydroxyl,                nitro,                halogenated alkyl having 1 to 8 carbon atoms,                halogenated alkoxy having 1 to 8 carbon atoms,                hydroxyalkyl having 1 to 8 carbon atoms,                hydroxyalkoxy having 2 to 8 carbon atoms,                alkenyloxy having 3 to 8 carbon atoms,                monoalkylamino having 1 to 8 carbon atoms,                dialkylamino wherein the alkyl portions each have 1 to 8 carbon atoms,                carboxy,                alkoxycarbonyl,                alkoxycarbonylmethyl,                alkylaminocarbonyl,                acylamido (e.g., acetamido),                acyloxy (e.g., acetoxy),                alkylthio having 1 to 8 carbon atoms,                alkylsulphinyl having 1 to 8 carbon atoms,                alkylsulphonyl having 1 to 8 carbon atoms,                oxo,                sulfo,                sulfonylamino,                cycloalkylamino wherein the cycloalkyl group has 3 to 7 carbon atoms and is optionally substituted by halogen (F, Cl, Br, or I, preferably F or Cl), alkyl having 1 to 8 carbon atoms, halogenated alkyl having 1 to 8 carbon atoms, alkoxy having 1 to 4 carbon atoms, amino, monoalkylamino wherein the alkyl portion has 1 to 8 carbon atoms, dialkylamino wherein the alkyl portions each have 1 to 8 carbon atoms, COR17, CSR17, cyano, hydroxyl, nitro, oxo, or thio,                aryl containing 6 to 10 carbon atoms (e.g., phenyl, naphthyl, biphenyl) and is optionally substituted by halogen (F, Cl, Br, or I, preferably F or Cl), alkyl having 1 to 8 carbon atoms, halogenated alkyl having 1 to 8 carbon atoms, alkoxy having 1 to 4 carbon atoms, amino, monoalkylamino wherein the alkyl portion has 1 to 8 carbon atoms, dialkylamino wherein the alkyl portions each have 1 to 8 carbon atoms, COR17, CSR17, cyano, hydroxyl, nitro, oxo, or thio,                aryl-alkylene group (e.g., benzyl, phenethyl, phenpropyl) wherein the aryl portion contains 6 to 10 carbon atoms and the alkylene portion contains 1 to 4 carbon atoms and is unsubstituted or substituted one or more times by halogen (F, Cl, Br, or I, preferably F or Cl), alkyl having 1 to 8 carbon atoms, halogenated alkyl having 1 to 8 carbon atoms, alkoxy having 1 to 4 carbon atoms, amino, monoalkylamino wherein the alkyl portion has 1 to 8 carbon atoms, dialkylamino wherein the alkyl portions each have 1 to 8 carbon atoms, COR17, CSR17, cyano, hydroxyl, nitro, oxo, or thio,                aryloxy wherein the aryl portion contains 6 to 10 carbon atoms (e.g., phenyl, naphthyl, biphenyl) and is optionally substituted by halogen (F, Cl, Br, or I, preferably F or Cl), alkyl having 1 to 8 carbon atoms, halogenated alkyl having 1 to 8 carbon atoms, alkoxy having 1 to 4 carbon atoms, amino, monoalkylamino wherein the alkyl portion has 1 to 8 C atoms, dialkylamino wherein the alkyl portions each have 1 to 8 carbon atoms, COR17, CSR17, cyano, hydroxyl, nitro, oxo, or thio,                arylthio wherein the aryl portion contains 6 to 10 carbon atoms (e.g., phenyl, naphthyl, biphenyl) and is optionally substituted by halogen (F, Cl, Br, or I, preferably F or Cl), alkyl having 1 to 8 carbon atoms, halogenated alkyl having 1 to 8 carbon atoms, alkoxy having 1 to 4 carbon atoms, amino, monoalkylamino wherein the alkyl portion has 1 to 8 carbon atoms, dialkylamino wherein the alkyl portions each have 1 to 8 carbon atoms, COR17, CSR17, cyano, hydroxyl, nitro, oxo, or thio,                cycloalkyloxy wherein the cycloalkyl group has 3 to 7 carbon atoms and is optionally substituted by halogen (F, Cl, Br, or I, preferably F or Cl), alkyl having 1 to 8 carbon atoms, halogenated alkyl having 1 to 8 carbon atoms, alkoxy having 1 to 4 carbon atoms, amino, monoalkylamino wherein the alkyl portion has 1 to 8 carbon atoms, dialkylamino wherein the alkyl portions each have 1 to 8 carbon atoms, COR17, CSR17, cyano, hydroxyl, nitro, oxo, or thio,                heterocyclic group, which is fully saturated, partially saturated or fully unsaturated, having 5 to 10 ring atoms in which at least 1 ring atom is a N, O or S atom, which is unsubstituted or substituted one or more times by halogen (F, Cl, Br, or I, preferably F or Cl), alkyl having 1 to 8 carbon atoms, halogenated alkyl having 1 to 8 carbon atoms, alkoxy having 1 to 4 carbon atoms, amino, monoalkylamino wherein the alkyl portion has 1 to 8 carbon atoms, dialkylamino wherein the alkyl portions each have 1 to 8 carbon atoms, COR17, CSR17, cyano, hydroxyl, nitro, oxo, or thio (e.g., furyl, thienyl, methylthienyl, bithienyl, benzylprazolyl, thiazolyl, imidazolyl, methylimidazolyl, pyrrolidinyl, morpholinyl, thiomorpholinyl),                heterocyclic-alkyl group, in which the heterocylic portion is fully saturated, partially saturated or fully unsaturated, having 5 to 10 ring atoms in which at least 1 ring atom is a N, O or S atom, and the alkyl portion is an alkylene group containing 1-4 carbon atoms, wherein said heterocyclic-alkyl group is unsubstituted or substituted one or more times by halogen (F, Cl, Br, or I, preferably F or Cl), alkyl having 1 to 8 carbon atoms, halogenated alkyl having 1 to 8 carbon atoms, alkoxy having 1 to 4 carbon atoms, amino, monoalkylamino wherein the alkyl portion has 1 to 8 carbon atoms, dialkylamino wherein the alkyl portions each have 1 to 8 carbon atoms, COR17, CSR17, cyano, hydroxyl, nitro, oxo, or thio (e.g., piperidinylethyl), or                                    combinations thereof;                                                                                R15 and R16 are each independently                    H,            Ar,            Ar-alkyl (e.g., benzyl, fluorobenzyl, methoxybenzyl, phenethyl, phenpropyl),            Het,            C1-4-alkyl (e.g., CH3) which is unsubstituted or substituted one or more times by F, Cl, Br, I, CN, OH, alkoxy having 1 to 4 carbon atoms (e.g., OCH3), monoalkylamino, dialkylamino (e.g., diethylamino), C3-8-cycloalkyl, or combinations thereof,            cycloalkyl having 3 to 10, preferably 3 to 8 carbon atoms, which is unsubstituted or substituted one or more times by halogen, hydroxy, oxo, cyano, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, or combinations thereof (e.g., cyclopentyl),            C3-6-alkenyl which is unsubstituted or substituted one or more times by F, Cl, Br, I, CN, alkoxy having 1 to 4 carbon atoms (e.g., OCH3), Ar (e.g., phenyl) or combinations thereof, or            C3-6-alkynyl which is unsubstituted or substituted one or more by F, Cl, Br, I, CN, alkoxy having 1 to 4 carbon atoms (e.g., OCH3), or Ar (e.g., phenyl) or combinations thereof;                        R17 is H,                    C1-6-alkyl (e.g., CH3) which is unsubstituted or substituted one or more times by F, Cl, Br, I, CN, OH, alkoxy having 1 to 4 carbon atoms (e.g., OCH3), NR15R16, SH, SR15, SOR16, C3-8-cycloalkyl, SO2R15, SO2NR15R16, Ar, Het, or combinations thereof,            C3-6-alkenyl which is unsubstituted or substituted one or more by F, Cl, Br, I, CN, OH, alkoxy having 1 to 4 carbon atoms (e.g., OCH3), NR15R16, SH, SR15, SOR15, C3-8-cycloalkyl, SO2R15, SO2NR15R16, Ar, Het, or combinations thereof,            C3-6-alkynyl which is unsubstituted or substituted one or more by F, Cl, Br, I, CN, OH, alkoxy having 1 to 4 carbon atoms (e.g., OCH3), NR15R16, SH, SR15, SOR15, C3-8-cycloalkyl, SO2R15, SO2NR15R16, Ar, Het, or combinations thereof,            C3-8-cycloalkyl which is unsubstituted or substituted one or more times by F, Cl, Br, I, CN, OH, alkoxy having 1 to 4 carbon atoms (e.g., OCH3), NR15R16, SH, SR15, SOR15, unsubstituted C3-8-cycloalkyl, SO2R15, SO2NR15R16, Ar, Het, or combinations thereof,            C4-8-cycloalkylalkyl which is unsubstituted or substituted one or more times by F, Cl, Br, I, CN, OH, alkoxy having 1 to 4 carbon atoms (e.g., OCH3), NR15R16, SH, SR15, SOR15, unsubstituted C3-8-cycloalkyl, SO2R15, SO2NR15R16, Ar, Het, or combinations thereof,                        m is as described above;        and        o is 1 or 2;or            R1 is
                wherein m is as described above.        
The compounds of Formula (1), described in WO 2005/063767, WO 2005/092890, WO 2005/111038, WO 2006/001894 and WO 2006/069097, are being studied to determine their potential as oral agents as a nicotinic α-7 receptor partial agonists, acting on a highly specialized receptor found in the central nervous system. Compounds that act on this receptor could be beneficial in the treatment of Alzheimer's disease and schizophrenia, as well as other psychiatric and neurological disorders.
Methods for the preparation of (1) are also set out in WO 2005/063767, WO 2005/092890, WO 2005/111038, WO 2006/001894 and WO 2006/069097, which disclose that compounds of Formula (1) can be prepared from the appropriate bicyclobase R1H, wherein R1 is as described above, and 5-(trifluoromethoxy)-1H-3-indazolecarboxylic acid (3), as shown below in Scheme 1.

Compound (3) is a key intermediate for the synthesis of compounds of Formula (1). A synthetic route for intermediate (3) is disclosed in WO 2005/063767, WO 2005/092890, WO 2005/111038, WO 2006/001894 and WO 2006/069097. This synthetic route involves a diazotization reaction of 5-trifluoromethoxyisatin in moderate yield. However, such aromatic diazonium salts (5) are not generally stable at temperatures above 5° C. (Richard C. Wedlich, Chemical Engineering Progress, October 2001), which makes them less suitable for large-scale preparations.

Accordingly, novel, efficient methods for preparing (3) are sought.